Method for reinforcing textile garments with thermosetting films

ABSTRACT

A process for reinforcing textile garments by forming a coherence of thermosetting or thermosettable reinforcing film in the fabric fibers of said garments at localized areas subject to severe stress is provided. The process is particularly applicable to permanent-crease slacks and like garments impregnated with a solution of resins polymerizable to a water-insoluble state and which provide for the permanent-crease. In the process, the thermosetting film is adhered and cohered to and with the surface fibers on one surface of the garment fabric by application of heat and pressure, cooled and the garment fabric is then optionally baked in an oven to polymerize the permanent crease resins and also to harden or post-cure the thermosetting reinforcing film. The thermosetting reinforcing film which may have a non-woven backing, used in the present invention has controlled flow characteristics and is so characterized that the appropriate combination of heat and pressure will cause the material to set up to a relatively rigid and non-flowable state after a few seconds thereby preventing bleeding through, but the flow will still be sufficient to provide for a good interlock and/or encapsulation of the thermosetting film and the fibers.

Unite States Patent 91 Rossell et al.

[451 Mar. 27, 1973 METHOD FOR REINFORCING TEXTILE GARMENTS WITH THERMOSETTING FILMS [75] Inventors: Gary L. Rosselll, Philadelphia; Paul C. Fleisher, Jr., Lafayette Hill; Maurice I. Seifer, Levittown, all of Pa.

[73] Assignee: Rohm and Haas Company, Philadelphia, Pa.

[22] Filed: Mar. 7, 1969 [21] Appl. No. 805,359

Related US. Application Data [63] Continuation-impart of Ser. No. 779,606, Nov. 27,

1968, abandoned.

Primary ExaminerH. Hampton Hunter 7 AtzomeyAlvin M. Esterlitz, Carl A. Castellan and George W. F. Simmons ABSTRACT A process for reinforcing textile garments by forming a coherence of thermosetting or thermosettable reinforcing film in the fabric fibers of said garments at 10- calized areas subject to severe stress is provided. The process is particularly applicable to permanent-crease slacks and like garments impregnated with a solution of resins polymerizable to a water-insoluble state and which provide for the permanent-crease. In the process, the thermosetting film is adhered and cohered to and with the surface fibers on one surface of the garment fabric by application of heat and pressure, cooled and the garment fabric is then optionally baked in anoven to polymerize the permanent crease resins and also to harden or post-cure the thermosetting reinforcing film. The thermosetting reinforcing film which may have a non-woven backing, used in the present invention has controlled flow characteristics and is so characterized that the appropriate combination of heat and pressure will cause the material to set up to a relatively rigid and nonflowable state after a few seconds thereby preventing bleeding through, but the flow will still be sufficient'to provide for a good interlock and/or encapsulation of the thermosetting film and the fibers.

8 Claims, 1 Drawing Figure METHOD FOR REINFORCING TEXTILE GARMENTS WITH THERMOSETTING FILMS This is a continuation-in-part of application Ser. No. 779,606 filed Nov. 27, 1968, now abandoned.

This invention relates to an improved textile garment and to a method for reinforcing the fabric of the garment to increase its wear or abrasion resistance and/or its tear resistance.

In recent years, much effort has been extended to improve the wear characteristics of textile garments.

Also, in recent years permanent-press and permanentcrease fabrics have entered the market place and taken an increasing share of the market. While the permanent-crease process and resins, for example see U.S. Pat. Nos. 2,974,432 and 3,268,195 (Koratron" Fabrics) are effective and provide a permanently pressed or permanently creased garment which will stand many washings, the resins themselves and the heat treatments required to throughly set them often deleteriously affect the fibers structure by weakening them and thereby decreasing the abrasion resistance of the finished garment. This is particularlynoticeable in areas of the garment or garments which are'subject to repeated stress such as the knees and elbows.

Numerous approaches have been taken in the past to provide for increasing the abrasion resistance and tensile strength of the textile fabric by treatment with a resinous material. However, in many instances, these prior treatments have been unsatisfactory for one reason or another. For example, laminated resin films heretofore adhered by heat and pressure to the surface of the fabric only, readily peel after the garment has undergone cleaning operations. The bonding strength of the resins to the surface of the fibers is incapable of withstanding repeated force applied to the garment during the washing process. Frequently, the laminating reinforced fabric also thickens and stiffens the film to such an extent that it is uncomfortable and inflexible to wear.

If more heat and/or pressure is applied to effect the lamination using such prior resin films, to cause the resin to melt and flow through the interstices in the textile fabric to completely encapsulate the fibers, the resin becomes visible in the garment, particularly if applied only to an isolated area, such as the knees in a pair of slacks, and thereby detracts from the appearance of the garment. Furthermore, with the interstices filled with resin, the garment fabric is rendered nonporous or at least substantially so, preventing or reducing evaporation of perspiration, and preventing or reducing and heat transfer-through the fabric thereby causing discomfort of the wearer.

Heretofore, many thermoplastic and thermosetting resinous plastic materials have been applied in solution or dispersions to fabrics either generally, or to reinforce specific areas, including both thermoplastic and thermosetting materials. However, as by coating of the fibers or fabric with the material by spraying, washing or dipping. Materials applied in this manner bleed or seep through the entire fabric and the interstices thereof. The fabric is substantially stiffened and the coating is visible, detracting from the appearance of the garment, particularly when it is applied to isolated areas of the gannent which are subjected to severe stresses, for example, the knee and elbow areas.

reinforced. Conklin teaches that the thermoplastic film must be only lightly or partly adhered in the first step, i.e., under the application of heatand pressure between 350 and 450F. and 20-to pounds per square inch for 4 to 15 seconds. Conklin further cautions thattoo much heat and/or pressure will cause melting and bleeding of the thermoplastic film through to the front or outer surface of the fabric or fiber surface. In the second step of the Conklin process the garment which is a permanent-press treated garment is baked in an oven in the temperature range of 275-450F. for approximately 20 minutes to (1) polymerize the permanent-press resins which have previously been padded into the fabric from an aqueous solution thereof and (2) cause the thermoplastic film to soften and flow and completely adhere to the fibers by wrapping around a major portion of the fibers adjacent the inner surface of the garment.

. The single FIGURE of the drawing is a rear view of a pair of trousers or slacks with a portion'of the fabric in the back of the garment cut away to expose the inside of the garment.

It has now been found that if a preformed thermosetting film is used as the reinforcing element and if the reinforcing thermosetting film has controllable flow characteristics and is applied under the proper conditions of heatand pressure that the bonding and adhering can be fully completed or at least substantially completed in one step without fear of bleeding of the film through or otherwise causing an unsatisfactory product. Of course, the baking step, while optional, may still be desirable particularly in the case of permanent press fabrics and additionally the baking optionally causes a final curing and/or hardening of the thermosetting film which is used in the present application. If no baking step is used, then the thermosetting reinforcing film can be bonded and cured all in one step.

' Preferably, the thermosetting film is a relatively soft, self-crosslinking and thermosetting acrylic film which is supplied on polyethylene or on a silicone-coated release paper in a roll, the film thickness being'from about 1 to 10 mils and preferably from 2 to 5 mils in thickness. Thermosetting films useful in the present invention are preferably colorless and transparent, soft and flexible and should provide a laminate which is durable to laundering and/or drycleaning and imparts a soft hand to the finished and reinforced fabric. The thermosetting films are, as heretofore indicated, supplied in a thickness of about l-10 mils,- and, more preferably in a 2- to 5-mil thickness. As supplied, the film on release paper is usually much larger in area than the area of the garment to be reinforced,'.and the film/release paper composite is thereforefirst cut into patch sizes. The film is transferred from the release paper, placed on the area of the paints, or other garments to be reinforced and bonded to the area to be reinforced under the application of heat and pressure. Various combinations of heat and pressure can be used with the thermosetting films of the present invention, to

achieve a good bond and cure. The temperatures, pressures and times of bonding will vary somewhat with the weight and type of fabric or garment and the dye used in the fabric or garment. There can be used bonding conditions comprising temperatures of about 200F. to about 375F., and more preferably temperatures in the range of about 275F. to about 350F.; times varying from about 3 to 35 seconds, more preferably 7 to 10 seconds; and, pressures of about to about 100 lbs. per sq. inch more preferably about 5 to about 15 lbs. per sq. inch. It should be noted that the bonding temperatures are significantly lower than those used in the prior art, e.g., in Conklin; thus there can be and is usually much lessrisk of dye-fade scorching of the fabric in the case of the thermosetting films used in present invention.

The thermosetting films useful in present invention comprise B-stage thermosetting materials, by which is meant they are fusible and insoluble but they are convertible into infusible and soluble insoluble C-stage materials under the application of suitable heat and transition temperature see I. Williamson, British Plastics 23, 87-90, 102 (1950)), which is not over 20C., and which will cure to a fully cured state in- 1 minute or less at 325F. The preferred therrnosetting materials useful in our invention will cure at 325F. in -20 seconds, and cure in gradually increasing times as the temperature is gradually reduced. Suitable thermosetting film materials, in addition to those having acrylic functionality as hereinafter set forth, include reactive polymers, based on styrene and monomers copolymerizable therewith, which have pendant reactive substituted groups such as carboxy, sulfo, amino, etc., all as more fully set forth in U.S. Pat. No. 3,215,647. As noted in that patent the reactive polymers may be further reacted with coreactive materials containing a methylol group, a modified methylol group which have been alkylated with an alcohol having one to four carbon atoms, etc. Examples of such coreactive materials are melamine, melamineformaldehyde condensates, guanidine, dicyandiamide etc.

As noted heretofore the thermosetting resin is preferably one which contains some acrylic functionality. More preferably, the preformed thermosetting film is a B-stage thermosetting film which contains (a) certain linear addition copolymers containing N-methylolamide groups and amide groups in certain proportions optionally combined with (b) an aminoplast as hereinafter defined, and optionally (c) with a catalyst such as ammonium thiocyanate or maleic acid as the curing catalyst. By the term maleic acid as used herein is meant maleic acid or compounds which yield maleic acid under the conditions of use, such as maleic anhydride.

The linear addition copolymers used in the composition of the present invention are water-soluble copolymers obtained by the emulsion copolymerization of the mixture of (a) from about l-20 percent by weight acrylamide or methacrylamide or the formaldehyde reaction products of said amide including methylol and methoxy-methyl derivatives with (b) at least one monomer selected from the group consisting of acrylonitrile, styrene, a-methyl styrene, vinyl toluene, vinyl acetate, and esters of the formula wherein n is an integer having a value of 1 to 2 and R is an alkyl group having one to 18 carbon atoms. Examples of the latter esters are methyl methacrylate, butyl methacrylate, methyl acrylate, ethyl acrylate, butyl acrylate, t-octyl acrylate and methacrylate and octadecyl acrylate and methacrylate. The monomers are selected so that the copolymer has an apparent second order transition temperature, T which is not over 20C. When monomers such as acrylonitrile methyl methacrylate, and styrene which produce homopolymers having T, values above 20C are used, the proportion thereof in the copolymer is limited to that which produces with the other monomers used in the particular copolymer, such as ethyl acrylate, methyl acrylate, or octyl acrylate, or methacrylate, a T, value of 20C. or less. The molecular weight may be from about 100,000 to 10,000,000.

When the amide component of the copolymer consists of a mixture of (1) either acrylamide or methacrylamide with (2) N-methylol a'crylamide or N- methylol methacrylamide, it is preferred that the two materials be used in a 1:1 molar ratio; although this is not essential. Where the amide is used by itself, it is preferred to use the methacrylamide. However, where a combination of amide and N-methylol amide is used, it is preferred to acrylamide and N-methylol acrylamide. The preferred copolymers are those which contain a mixture of amide and N-methylolamide. It is preferred to have from l-6 percent by weight of the amide component in the copolymer.

The method of preparation of the emulsion copolymer used in the present invention is described in U.S. Pat. No. 3,033,811 to Brown et al. and U.S. Pat.

No. 3,157,562 to Kine et al., which disclosures are incorporated herein by a reference hereto. These linear addition copolymers are combined, optionally, with an aminoplast condensate as disclosed in the latter of these patents. The arninoplasts suitable for use with the linear addition copolymer in the practice of the present invention are water-soluble, heat-convertible methylol derivatives of urea, cyclic ethylene urea, cyclic propylene urea, thiourea, cyclic ethylene thiourea, melamine, alkylmelamine, arylmelamines, arylquanamines, quanamines, alkylquanamines, and mixtures thereof. Generally speaking, water-soluble resins can be prepared according to one of the following processes: 1) controlled reaction conditions so that the degree of polymerization is kept very low, even to the monomeric stage, and 2) introduction ofhydrophilammonium hydroxide, 0.5 parts of a 25 percent aqueous solution of ammonium thiocyanate catalyst and 18.75 parts of a 4 percent aqueous solution of methyl cellulose having a viscosity of 4,000 cps.

The mixture is cast onto polyethylene and siliconecoated kraft release paper using a knife coater and dried for about 15 minutes at a temperature of 150 to 180F. to give a preformed thermosetting reinforcing film of 2 mils thickness. The film on release paper is rolled and ready to be cut to appropriate size for use in specific reinforcing applications.

A sample of the thermosetting film on release paper having a suitable size is bonded to an area of a cotton broadcloth fabric, which is intended for manufacture into garments such as shirts or slacks, the area being one which will be subject to more stress than other areas of the fabric. The thermosetting film is bonded to the cotton broadcloth using a pressure of 5 psi, a temperature of 320 F. and a time of 7 seconds. These conditions provide an excellent bond of the reinforcing film and fabric fibers. The release paper is removed and the reinforced fabric is post-cured at 300 F. for 10 minutes. The post-cure merely hardens the film and does not cause any additional flow thereof. The table below shows the dramatic increase in abrasion resistance of the reinforced fabric as compared to the cotton broadcloth without reinforcement.

TABLE A Cycles to Failure Using a Wyzenbeck Abrader, Broadcloth Abraded Against Duck Cloth Cycles Cotton Broadcloth Control 2,000 (hole developed) Cotton Broadcloth rein- 10,000 (some wear apparent) forced with thermosetting (but no hole) It can be seen from the table above thatthe abrasion resistance of the cotton broadcloth increased by at least a factor of five. Also, the film remains intact through multiple washings and drycleanings.

Similar results are obtained without the ammonium thiocyanate catalyst.

EXAMPLE B Using the preformed thermosetting film of Example A above, the knee area of a pair of slacks of 65 percent Dacron polyester and 35 percent rayon which is pretreated with a permanent-press resin, as disclosed in the Warnock patents heretofore mentioned, is reinforced by bonding the thermosetting film to the knee area of the inner surface of the fabric for 7 seconds at 320F. and 5 psi. The slacks were washed in a Maytag washer at 140F. with Tide detergent. The appearance of the slacks and the condition of the patched or reinforced area without any post-cure, after 40 washes is excellent. Another pair of slacks is post-cured at 320F. for l0 minutes and the appearance of the slacks and patched area is the same after 40 washes as the nonpost-cured fabric. The slacks lasted 2,167 cycles to break in a Stoll Flex Abrasion test, an increase of 42 percent over the same slacks with no reinforcement at all being present.

The preformed thermosetting film can be applied to other fabrics and garments and at lower temperatures if desired (e.g. 250F.) for example, to school and play pants of 50 percent polyester 50 percent cotton, with similar improved results in abrasion resistance in the reinforced areas and with good durability, i.e'., retention of good properties and maintenance its reinforcement effect after numerous washes and/or drycleanings.

EXAMPLE C An aqueous dispersion containing 60 percent solids of an emulsion copolymer of about 85.9 percent ethyl acrylate, 10 percent acrylonitrile, 1.7 percent acry lamide and 2.4 percent methylolacrylamide is prepared by emulsion copolymerization. To parts of this dispersion are added 9.2 parts of a 70 percent aqueous solution of penta(methoxymethyl)melamine, 1 part of ammonium hydroxide and 18.75 parts of a 4 percent aqueous solution of methyl cellulose having a viscosity of 4,000 cps.

The above mixture is cast onto polyethylene and onto silicone-coated kraft release paper and dried for about 15 minutes at to F. to give a preformed thermosetting reinforcing film of about 2 mils thickness on the release paper. The filml-release paper combination is then laminated onto a 5 mil thick non-woven rayon fabric by passing the combination and nonwoven rayon backing through pressurized rolls. The non-woven/thermosetting film laminate (about of about 6-mil thickness) is then stripped from the release paper and is applied to the area of the garment or fabric to be reinforced by laying the film surface of the laminate against the inner surface of the area to be patched of reinforced. This leaves the non-woven surface in a position to contact the leg or other area of the wearer.

The non-woven/film composite or laminate is used to reinforce the inside knee area of a pair of boys play pants by bonding thereto at 320F. for 7 seconds at 5 psi. The pants show increased abrasion resistance and, in addition, there is a pleasant fabric-like feel sensed by the knee of the wearer even on very cold days or on hot, humid days. Also, the tear strength of the pants in the reinforced areas is improved by the non-woven/film composite or laminate when compared to reinforcement by the film alone.

EXAMPLE D The aqueous dispersion given in Example C above is cast on the polyethylene and on silicone coated kraft release paper and dried for about 15 minutes at about 150 to 190F. to give a preformed thermosetting or thermosettable reinforcing film of about 2 mils thickness on the release paper. The film/release paper combination is then laminated onto a 3-4 mil thick tissue paper supplied by the Peerless Paper Mill of Oaks, Penna. The paper is 13 pound basis weight paper (500 sheets at 24 inches X 36 inches) with a unit weight of 0.039 lbs. per sq. yard. Lamination is carried out by passing the film/release paper combination and the tissue paper through pressure rolls operated at about 15 tons pressure and at a temperature in the range of from about 75 to 270F. The paper/thermosettable film laminate is then stripped from the release paper and is applied to the garment or fabric area to be reinforced by laying the film surface of the laminate against the ic groups into the molecules of the polymeric condensates. Thus, water-soluble, heat-convertible aminoplasts such as dimethylol urea and trimethylol melamine can be prepared by careful control of reaction conditions as set forth in Schildknecht, Polymer Processes, Vol. X, page 305 etseq. (Interscience Press, 1956). Such simple methylol derivatives frequently exhibit limited solubility in cold water, and are not particularly stable on prolonged storage, tending to polymerize to water-insoluble polymers.

A preferred class of water-soluble aminoplasts are the condensates of formaldehyde and the reaction products of urea and/or melamine with a lower alkanol, such as methanol. These condensates are heat-convertible to insoluble crosslinked polymers. Thus, the condensates of methoxymethylureas and formaldehyde and methoxymethylmelamines and formaldehyde are particularly suitable for the films of the present invention. The preparation for ethylene urea derivatives, such as N,N' bis(methoxymethyl) ethylene urea is set forth in detail in U.S. Pat. No. 2,373,136. The preparation of methylol methoxymelamine is set forth in Schildknecht, ibid, page 340. The preparation of methylolmethoxy melamines is set forth in US. Pat. No. 2,529,856 and the data set forth therein are incorporated by reference. The preparation of another class of compounds suitable in the present invention, such is N,N' bis(methoxymethyl) urea as set forth in Bull. Chem. Soc. Japan, Vol. VI, no. 3,239 (1936).

In an alternative embodiment of our invention, the preformed thermosetting reinforcing film is backed with or laminated to a non-woven or filamentous product and the film/ non-woven composite used to reinforce the garment in a manner similar to that described with reference to the preformed thermosetting film per se. The non-woven backing provides a more fabric-like feel to the wearer of the garment, in the areas where reinforcement takes place, and in addition to reinforcement by increased abrasion resistance, there is also provided increased tear resistance.

The non-woven backing or fibrous web may be formed in any suitable manner such as by carding, garnetting, or by dry deposition from an air suspension of the fibers. The thin web or fleece obtained from a single card may or may not be treated with a binder generally it is necessary and desirable to superpose a plurality of such webs to build up the mat to sufficient thickness for the end use intended. ln building up such a mat, alternate layers of carded webs may be disposed with their fiber orientation directions disposed at 60 or 90 angles with respect to intervening layers.

The fibers from which the webs may be made include cellulosic fibers such as cotton, rayon, jute, ramie, and linen; also cellulose esters such as cellulose acetate; silk, wool, casein, and other proteinaceous fibers; polyesters such as poly(ethylene glycol terephthalate); polyamides such as nylon; vinyl resin fibers such as the copolymer of vinyl chloride and vinyl acetate, and polymers of acrylonitrile containing 70 percent to 95 percent by weight of acrylonitrile including those available under the trademarks Orlon and Acrilan. Any of the bonded non-woven webs disclosed in Kine et al.,

U.S. Pat. No. 3,157,562, may be used as the backing for the preformed thermosetting film and the resulting composite used to reinforce garments in accordance with the present invention. The preformed thermosetting reinforcing film is laminated or married" to the non-woven web between pressure rolls, with or without heat, prior to application of the composite as a reinforcement for garments. The overall thickness of the preformed thermosetting film/non-woven composite is in the range of about 3 to about 20 mils. ln a typical example, a 2-mil preformed thermosetting film is married or laminated to a rayon non-woven backing of S-rnil thickness by passing the film and web together through a pair of pressure rolls; the composite has a thickness of 6 mils.

The non-woven backings may also be a paper formed of a good grade of wood stock. While any non-woven paper backing of various densities can be used in the present invention, it is preferred to use a relatively light-weight paper such as toilet tissue paper, facial tissue paper of the type available under the trademark Kleenex, and wiping tissue of the type available under the trademark Kim-Wipe. These papers may be made with or without added wet-strength resins. The thickness of the paper used in the present invention ordinarily will vary between about 1 mi] and 15 mils with the overall range of the film/paper composite being in the range of about 3 to about 20 mils. The non-woven paper reinforcing film is particularly useful for some of the lighter fabrics where the shrinkage problem might occur. That is, it has been noted that with some textilebacked reinforcing film there is a differential shrinkage between the film and the fabric to be reinforced. This difference of shrinkage results in a puckering at the patched area which is objectionable from an aesthetic point of view. The paper-backed reinforcing film overcomes this particular problem.

The FIGURE of the drawing illustrates this preferred embodiment and shows a pair of slacks 3 having trouser legs 5 creased along lines 6 and cut away in the rear at 7. The figure shows the fly 4 and two reinforcing patches 8a and 8b fastened to the inside wall of the legs of the slacks. The reinforcing patch secured to the left leg is shown as a simple reinforcing film with the fabric showing through the film whereas the patch 8b secured to the right leg consists of a laminate formed of a thermoset film one face of which is adhered directly to the inside wall of the trouser leg and the exposed face thereof carries adhered thereto a thin non-woven web as indicated by the stippling so that the leg of the person wearing the trousers or slacks will come into contact with the fibrous layer of the laminate thereby providing a desirable textile feel. Both patches 80 and 8b may consist of a thermoset film or both may be formed of the film/ fibrous web laminate.

To assist those skilled in the art to practice this invention, the following modes of operation are given in which all parts and percentages are by weight unless otherwise specifically noted.

EXAMPLE A An aqueous dispersion containing 46 percent solids of an emulsion copolymer of about 85.9percent ethyl acrylate, 10 percent acrylonitrile, 1.7 percent acrylamide and 2.4 percent methylol acrylamide is prepared by emulsion copolymerization. To parts of this emulsion are added 7.1 parts of a 70 percent aqueous solution of tris(methoxymethyl)melamine, 1.2 parts of inner surface of the area to be patched or reinforced. This leaves the non-woven tissue paper surface in the position to contact the leg or other area of the wearer. Garments which have been reinforced with the paper/film composite show increased abrasion resistance and, in addition to improved asethetic qualities, the patch does not show any puckering after 16 washes in a Maytag washer operated with Tide detergent at a temperature of about 140-160F. Tear strength, as indicated in Example C, is also improved with the by the paper/film composite.

We claim:

1. A textile garment including, adhered on a portion of a surface thereof which is subject to more stress than other areas or portions of the garment, a preformed laminate, having an overall thickness of about 3 to about 20 mils, of a thermosetting film of about 1 mil to about 10 mils thickness and a non-woven web, one surface of the film being permanently adhered directly to the garment surface and the web being permanently adhered to the other surface of the film by virtue of the thermoset condition of the film.

2. A textile garment according to claim 1 in which the non-woven fibrous web is disposed on a side of the garment which normally comes into direct contact with the wearer of the garment.

3. A textile garment according to claim 2 in which the non-woven fibrous web is rayon.

4. A textile garment according to claim 1 in the form of a pair of slacks containing a permanent-crease resin and having at least one crease applied thereto prior to curing of the permanent-crease resin.

5. A garment according to claim 1 in which the nonwoven web is a tissue paper having a thickness of l to 15 mils.

6. A textile garment according to claim 5 in which the paper is disposed on a side of the garment which normally comes into direct contact with the wearer of the garment.

7. A textile garment according to claim 6 in the form of a pair of slacks containing a permanent-crease resin and having at least one crease applied thereto prior to curing of the permanent-crease resin.

8. A garment according to claim 6 in which the thermo-setting film is a copolymer of N-methylolacrylamide or of N-methylolmethacrylamide. 

2. A textile garment according to claim 1 in which the non-woven fibrous web is disposed on a side of the garment which normally comes into direct contact with the wearer of the garment.
 3. A textile garment according to claim 2 in which the non-woven fibrous web is rayon.
 4. A textile garment according to claim 1 in the form of a pair of slacks containing a permanent-crease resin and having at least one crease applied thereto prior to curing of the permanent-crease resin.
 5. A garment according to claim 1 in which the non-woven web is a tissue paper having a thickness of 1 to 15 mils.
 6. A textile garment according to claim 5 in which the paper is disposed on a side of the garment which normally comes into direct contact with the wearer of the garment.
 7. A textile garment according to claim 6 in the form of a pair of slacks containing a permanent-crease resin and having at least one crease applied thereto prior to curing of the permanent-crease resin.
 8. A garment according to claim 6 in which the thermo-setting film is a copolymer of N-methylolacrylamide or of N-methylolmethacrylamide. 